HCID 10509227, compound → HCID 178454496, compound

HRID 1901980Notes

Reaction equation

[CH3:1][C:2](=[CH2:56])[C:3]([NH:5][C:6]1[N:7]=[C:8]([CH2:53][CH2:54][CH3:55])[N:9]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[N:33](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:32]=[N:31][N:30]=3)=[CH:19][CH:18]=2)[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:4].Cl.C(O)C>>[CH3:56][C:2](=[CH2:1])[C:3]([NH:5][C:6]1[N:7]=[C:8]([CH2:53][CH2:54][CH3:55])[N:9]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]3[NH:30][N:31]=[N:32][N:33]=3)=[CH:19][CH:18]=2)[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:4]

Participants

Reactant 2

HCID 10509227HCID 10509227, compound

HCID 21887872Ethanol hydrochloride

Product 1

HCID 178454496HCID 178454496, compoundYield 42.2%

Conditions

Temperature: 90 °C

Procedure

To 250 mg of ethyl 4-[N-(2-methylacryloyl)amino]-2-n-propyl-1-[[2'-(N-triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyl]imidazole-5-carboxylate was added 10 mL of 2N-HCl-ethanol (1:1) and the mixture was stirred at an external temperature of 90° C. for 4 hours. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (chloroform-methanol=20:1) and recrystallized from acetonitrile to provide 71 mg of ethyl 4-[N-(2-methylacryloyl)amino]-2-n-propyl-1-[[2'-(tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-imidazole-5-carboxylate (yield 42%).

Workup

distillationThe solvent was then distilled off under reduced pressure
customthe residue was purified by silica gel chromatography (chloroform-methanol=20:1)
customrecrystallized from acetonitrile

Sources & evidence

ORD record: ord-41b8fdc124a642a9bad6da5d9fdc92e1
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05578733

Reaction notes

Loading…